Feels Like the First Time
by Enticingly
Summary: Everything's all wrong and Dean doesn't know how to fix it. Wincest. Read the warnings before reading, please. I don't want to offend.


**Warnings**: Jailbait, masturbation, anal, and some very very light kinks. Wincest.

My first time writing smut, so reviews are definitely appreciated. And if you want to give me any sort of prompt for my next story, I'm open to requests.

Enjoy.

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Sam was eleven years old and, in a rare and possibly unfortunate way, a normal boy going through the normal stages of puberty. His voice randomly made an awkward squeak while he was speaking, hair was growing in places he didn't really know hair could grow; his body was changing, and it scared the shit out of him. Dean, of course, found it all kinds of amusing. He was only fifteen and barely at the peak of his own puberty, but it was still fun to tell him "Well how about that, Sammy. You actually _are_ a boy after all."

Despite all the teasing and laughing when Sam punched him as a result of it, Dean really was looking out for his brother. He knew how awkward everything became and how difficult it was to get by while trying to figure out what was happening all on his own. If he could do anything to help it, he wouldn't let Sam go through the same thing. Take care of Sammy, just like always.

One night, sometime around two in the morning, Dean woke up to stifled sniffling coming from the small boy sleeping at his back. He instantly went into mother-hen mode and rolled over, "Sammy?" It was dark and hard to make out, but Sam was halfway curled up into a ball, biting his lip and near tears. Following his arms down the length of his body, it only took a few seconds for Dean to figure out what was going on.

Sam had his first wet dream and was having his very first hard-on.

He was very literally trying to shove himself back down, which only put pressure on his cock and made him make those pathetic little whimpering noises. Dean's mind was completely wiped blank. "It hurts, Dean." Three words and that miserable look in Sam's eyes, and Dean already knew what he had to do. His kid brother, the one he'd dedicated his whole life to protecting, was in pain and looking up to him for help. He was just helping him so he wouldn't be in pain anymore. That wasn't weird, right? He was just helping. Not weird at all.

Except no, it was definitely weird, especially since Dean didn't even _mind_.

"It's okay, Sammy," he whispered, "Here, just like this." And he reached down to take one of Sam's hands and wrap it around his dick, pausing a little when Sam's breath hitched and he almost cried out. "Shh, you can't wake Dad or he'll kick both our asses." Sam nodded and put his free hand, now balled into a fist, in his mouth so he could bite down on it as Dean started to pump his hand around him. Up and down, a good, smooth rhythm, and Sam was gasping and thrusting up into his hand beneath Dean's.

Dean just marveled in watching Sam's face. His eyes were tightly clenched, lost in his own pleasure, and Dean thought briefly, '_I'm doing this. I'm helping my baby brother jerk off. What the hell is wrong with me._' Just then, Sam's breathing started to pick up and he pulled his hand out from under Dean's to cling to his older brother's shirt. It was all over then, all lines crossed, as Dean's hand was now bare on Sam's cock, nothing in between and _fuck_, there was so much wrong with that but he didn't stop pumping. Sam was close then. Just a little more and then they could forget this ever happened.

As Sam came all over Dean's hand, Dean memorized the way his body jerked and his eyes flew open, hazel eyes looking for green eyes, and there was something just so wrong with that.

Almost immediately, Sam sank back into his pillow and conked out, exhausted from his first ejaculation. Quietly, so as not to wake him, Dean slid out of the bed and into the bathroom, hurriedly cleaning Sam's cum off of his hand. His heart was racing, mind replaying what just happened over and over again, and Dean was harder than he ever remembered being. It was fucked up and wrong and he almost started crying right then and there. But instead, he sat down on the toilet and started relieving himself to thoughts of Sam's body covered in a thin film of sweat, pulling on his shirt and biting so hard into his hand that Dean worried it would draw blood. He worked himself quickly, hating himself more and more with every second he though of his brother, but froze into stone when the bathroom door opened.

Sam poked his head inside and looked over to him, "Dean?" and just hearing him say his name was almost enough to make him come.

"Fuck, Sam, what the hell are you doing?" Dean tried to bark, inwardly cursing himself for the way his voice came out husky and strained.

Instead of walking away like Dean hoped he would, Sam stepped all the way into the bathroom, "Are you hurting too?' And _holy shit_, Sam was sitting on the bathroom floor in front of him now, reaching out to take Dean's cock into his hand.

"Stop, Sammy, no-" but it was too late, and his brother's tiny eleven year old hand was replacing his own, moving in awkward and uneven pumps and it didn't even matter 'cause holy _fuck_, it was _Sam_. Dean let out a moan and rolled his head back against the wall behind the tank, trying hard to imagine the last girl that did this to him instead of his baby brother. Then the worst thing happened.

Absolute horror struck Dean like lightning because _oh my God_, Sam had his cock in his mouth.

He didn't really know what he was doing, had only started sucking out of sheer curiosity, but none of that mattered in the slightest. Fireworks were going off in Dean's mind, his vision blurring and it was so wrong but it felt so fucking _good_. "Sam. Sammy," he gasped, reaching down to snake a hand into his brother's hair as his head bobbed up and down his length. He was so close to coming and he couldn't stand it. "Stop. Stop, you can't-"

A twenty four year old Sam looks up at his brother from his kneeled position between Dean's legs, cheeks flushed and lips puffy and red from sucking his cock. Instead of a bathroom floor, they're on one of the queen sized beds in some shoddy motel in the middle of God knows where, naked, lustful, and a lot more experienced than the memory Dean was just snapped from. "You want me to stop?" he asks, a little bewildered and Dean almost laughs.

"_God_, no. If I could have it my way, you'd never stop." A small pause, because then Sam's grinning like a dork which sends pleasant little chills down Dean's spine. "No, I just. I don't wanna come in your mouth tonight."

Fully dilated eyes meet up with Sam's suggestively and the younger brother sits up, "No way, man. We've gotta drive five hundred miles to Ohio tomorrow. I don't wanna be sore the whole time."

"Oh, c'mon, Sammy. You know I'll be gentle."

Sam raises an eyebrow skeptically, "That's what you said last time. And the time before that, and the time before that. You're _never_ gentle, Dean."

Dean smirks a little, "Yeah, but only because I know you like it like that." And then Dean knows he's won, because Sam's entire face flushes the brightest of reds and Dean takes the opportunity to flip him underneath him. Sam might be taller and wider than his older brother, but Dean's always been the stronger, more dominant one. And once he's got him like this, it's damn near impossible for Sam to deny him.

But only damn near. "Dean, _no_." He decidedly ignores the protesting and leans in to bite playfully at the hollow below Sam's neck, which draws a wonderful little gasping sound from his lips. "_Dean_," and now he's not fighting him off but urging him on and Dean grins victoriously against his brother's skin. He kisses Sam deeply, tongues searching the insides of mouths they already know like the backs of their hands, and he only pulls away when they need to breath. But he doesn't stop there, just goes straight to sucking lightly at the sensitive skin of Sam's neck, biting at his collarbone and _God_, are the noises Sam's making like music to Dean's ears.

As he works his way down the length of Sam's body, his fingers brush lightly over every inch of his skin, learning every crease and contour like they haven't been doing this for thirteen years. It leaves trails of sensation that burn like fire and Sam twists and writhes in ways that should be fucking illegal. It's wrong and wonderful and Dean can't get enough of it. When he finally takes Sam's cock in his hand, he's already harder than a rock and dripping with pre-cum.

"Dean, Dean, _please_."

"I know, Sammy. Just like this." And Sam moans his brother's name loudly as Dean starts moving up and down, the same perfect rhythm he showed him that very first time so long ago. It works every time, Sam clenching his eyes shut and biting on his fist out of habit. He's pretty sure he's ruined his baby brother forever and earned them both fast-pass tickets to Hell, but if they're going down, they're going down together. Dean reaches up with his free hand to pull the fist out of Sam's mouth, "How many times I gotta tell you? I wanna hear that pretty voice of yours."

Sam growls in response, then pulls Dean in for another kiss as an act of defiance. Dean doesn't mind. It's messy and desperate and if he doesn't get to fuck Sam soon, they're both gonna go crazy. He pulls away and puts those lips to better use elsewhere, sending Sam's head slamming back down into the pillows. Now working Sam's cock with both his fist and his mouth, Dean knows there isn't much time left. He grabs a small tube from the nightstand with his free hand and struggles to open it and slick two of his fingers up before pressing them gingerly into his younger brother.

"God, _fuck_, Dean!" And they aren't cries of pain but rather way too much goddamn pleasure, but Dean can't take anymore. No more teasing, no more playing around; he needs Sam, and he needs him _now_. But he promised to be gentle, so he works him quickly but softly, spreading him open like it's their first time again, which sends Sam over the edge. He sits up suddenly, eyes searching desperately for Dean's, and they meet just as Sam comes into Dean's mouth.

Not wasting even one second, Sam pulls him into a long kiss again, grinding his hips encouragingly as Dean positions himself properly above him. He pulls out his fingers and Sam gasps against Dean's lips, then inhales deeply when they're replaced with something much larger. The same even rhythm, but it's different and better and _worse_ and Dean hates that he loves every thrust and gasp and whimper. Sam's dragging his nails across Dean's back; Dean's biting into Sam's neck; everything is getting brighter and louder and holy good God, could this be any more perfect?

And there's something just so very, very wrong about that thought.

Sam won't stop crying Dean's name and Dean's having trouble processing anything beyond '_Sam, Sam, this is Sam, I'm inside Sam_', but through it all, something else is happening too. He can't stop thinking about that first time he helped his little brother relieve himself. Or two years later when they did it again in the Impala while John was out killing something. Or less than a few months after that when Dean fucked Sam for the very first time, and then cried himself to sleep when he heard John stumble in the door a few hours later. Dean can't stop thinking about every time he's laid his hands on Sam and how wrong all of it is, and there's something even worse about this time above all the rest. He doesn't know what. He doesn't know why. But just before he comes inside of his brother for what must be the millionth time, he leans down and whispers in Sam's ear.

"I love you, Sammy."

It's the first time he says it, and it won't be the last, but it stops Sam in his tracks and he cries out his brother's name one last time before the world catches fire and everything is very, very right.


End file.
